When she arrives in town on Monday for her first broadcast on Canadian soil, Oprah Winfrey will try to forget the most daunting challenge of her life.

The two sold-out shows at the Metro Toronto Convention Centre, the latest stop in “Oprah’s Lifeclass: The Tour,” will feature Winfrey as most TV viewers remember: laughing, bubbly, confident, powerful, in control. She will dole out “life lessons.” She will gab with a slate of inspirational speakers. She will joke with the audience and mug for the cameras.

But as she basks in thundering adoration, she will be standing at the edge of a precipice, one that was unseen during her astonishing run on broadcast television for a quarter-century.

The media mogul, with an estimated net worth of $2.7 billion, has watched in recent months as skeptics and critics have nickel-and-dimed her once sterling reputation. In describing OWN: Oprah Winfrey Network, her sputtering 15-month-old cable channel, they have used words no fan can remember: mismanaged, unfocused, bland, doomed, out of control.

Now industry whispers hinge on a single question: Can Oprah Winfrey save the network that bears her name or are we witnessing the end of an era?

When OWN was announced
, a joint venture between Winfrey’s Harpo Inc. and Discovery Communications Inc., expectations soared. Many believed this would be the most successful launch of a cable network in American history.

Winfrey, now 58, had perfected the daytime talk format while turning her syndicated show into a global brand. She would be joining forces with one of the savviest media companies in cable television, the deep-pocketed owner of stations such as TLC and Animal Planet.

But from the start, there were problems.

One former insider, speaking on the condition of anonymity due to a confidentiality agreement, said OWN’s seemingly can’t-miss prospects were dashed early by a “clash of cultures.” Winfrey loyalists and those not from Harpo were often at odds over basic strategy. This created an atmosphere of inertia and uncertainty.

“People can live with working with people they don’t like,” says the insider. “But this was just a lack of focus on what the channel should be.”

The initial brand positioning was clear: OWN would be the cable equivalent of Winfrey’s popular O Magazine. In fact, when Discovery chief executive David Zaslav first approached Winfrey with the concept, he was armed only with a persuasive smile and a copy of O.

So content would be aligned with her advice to viewers to “live their best lives.” What the network would not be, the insider stresses, “is the Church of Oprah, 24/7.” This idea is contrary to the prevailing criticism of OWN, which is that Oprah does not have enough of an onscreen presence.

The truth is, she was never supposed to.

There was another issue: some executives from Harpo, a production house that made millions from one syndicated show, had little to no experience running a cable network.

Lisa Erspamer, an executive producer with The Oprah Winfrey Show, relocated to Los Angeles from Chicago in 2009. She became OWN’s chief creative officer, a position Winfrey had mainly created for her star protégé. While Erspamer technically reported to chief executive Christina Norman — the former head of MTV Networks who was fired from OWN in May — the actual hierarchy was clear to everyone around the boardroom table.

Erspamer was a powerful figure inside Harpo. She mingled with A-list celebrities like Tom Hanks and masterminded some of Winfrey’s most memorable episodes, including the mass giveaway of Pontiacs in 2004.

But after joining OWN, according to another former employee, her devotion to Winfrey became a stumbling block for baffled co-workers.

“It was very cultlike,” says the former employee. “Lisa became the mouthpiece for Oprah. She would say, ‘Oprah wouldn’t like this’ or ‘Oprah wouldn’t do that.’ And it just became an arbitrary signal that you couldn’t do something. The way they operated was very, very different than the way you would typically run a network.”

Erspamer, who left the network earlier this year “by mutual agreement,” was forced to speak on Winfrey’s behalf because her boss was mostly MIA before OWN’s launch on Jan. 1, 2011. Winfrey was in lockdown mode, swamped with work as her show ended with epic fanfare in May.

“I think their (Discovery’s) expectations were she would be much more intimately involved with the network and she wasn’t,” says Steve Lanzano, president of TVB, the not-for-profit trade association of the U.S. commercial television industry.

“She’s a brand. But just because you brand a network, it does not mean your viewers are going to follow you if you are not there.”

For those who did follow, any sense of giddy reunion was quickly replaced by confusion. Instead of seeing Oprah, they were blitzed with a haze of insipid reality shows, old movies and half-baked service programs packaged between a few original series, including The Gayle King Show, Cristina’s Big Bowl of Love, Your OWN Show, Ask Oprah’s All-Stars and In the Bedroom With Dr. Laura Berman.

“The problem is that people want to see Oprah,” says Libby Gill, a brand strategist and former television executive. “I think they overestimated the power of Oprah’s draw when she’s not the main attraction.”

So when Winfrey’s show ended in the spring, she was under severe pressure to pilot the ship out of choppy waters. Discovery is providing the investment funding for OWN, which is supposed to be repaid when the network turns a profit. But Discovery has already spent more than $310 million (U.S.), well in excess of its initial commitment of $189 million.

Winfrey, meanwhile, is gambling with something arguably more valuable than her money: she is doubling down on her reputation and jeopardizing her legacy.

“If I knew then what I know now, I might have made some different choices,” she told CBS in an interview this month. “I would say if I were writing a book about (OWN), I could call the book 101 Mistakes.”

Winfrey also said she never felt better about the future. This optimism is shared by OWN co-presidents Erik Logan and Sheri Salata, and the top brass at Discovery.

But it only crystallized after the most difficult day of her career.

Oprah Winfrey
has personally fired only one person in her life.

When it happened, she bawled more than the terminated employee. So on the morning of March 19, Winfrey delayed her arrival at OWN headquarters, where as of July she had served as chief executive.

Maybe she didn’t want to cry again.

Outside on Wilshire Blvd., it was business as usual in sunny Los Angeles. But inside OWN, months of executive turnover, financial hemorrhaging, content screw-ups and rating failures were about to give way to a cyclone that, according to sources, was first planned in December.

When the debris had settled, 20 per cent of the OWN workforce was gone.

“It was sombre,” says one former employee. “People were in shock.”

Winfrey appeared after an HR team informed the 30 affected workers of the layoffs. Flanked by Logan, who joined Harpo in 2008 and quickly became a trusted member of her inner circle, Winfrey convened a “town hall.”

As a source familiar with the meeting quips: “It was the first time she was not treated to spontaneous applause when entering a room full of employees.”

The first four rows remained empty as rattled staff sat near the back and Winfrey explained the need for cutbacks and restructuring. When the town hall ended, no questions were asked.

“That was a very hard day for the network,” says Logan. “When you lose 30 employees, that wasn’t easy. What I think made it a little more challenging for all of us is the fact that those employees deeply cared for the mission that we were on.”

The mission would now have new ground rules.

“They would spend so much money,” says a former employee. “It was just a lack of experience, to be honest with you. (Erspamer) had never run a network before or had to produce shows on a budget.”

One of the problems, says a source familiar with the current situation, is that previous management built a larger than necessary staff for a startup. More troubling, they did not tap into the “back end resources” at Discovery. The companies will now “share” several departments, including finance, human resources, business affairs, research and marketing.

Just three days before the layoffs, there was another high-profile firing: Rosie O’Donnell, whose eponymous talk show was once heralded as the network’s most promising gambit, was shown the door after five months of dismal ratings.

OWN took a massive publicity hit. But the network emerged on less perilous footing.

Between the layoffs and cancellation, Discovery slashed close to $50 million from OWN’s bloated cost structure. A couple of weeks later, the network signed a significant distribution deal with Comcast Corp., which puts OWN in about 4 million new U.S. homes, boosting total market penetration to about 85 million. Meanwhile, first-quarter ratings are up 21 per cent, from 149,000 to 180,000 total viewers.

“We are 1,000 per cent committed to this business,” says David C. Leavy, chief communications officer at Discovery, when told every analyst interviewed for this story offered a grim prognosis for OWN. “We are in it for the long haul. Any other comments are ill-informed. We are more committed and more bullish about the business that we are building today than we ever have been.

“If this thing is not to succeed,” he adds, “then one has to assume that Oprah Winfrey and Discovery Communications can’t find a hit or two a year to develop for this network. I like our chances.”

This is where the debate gets muddy.

Cable and broadcast
television are very different beasts.

A hit show on cable will never have the same audience size as a hit show on broadcast for several reasons, including scale. But unlike broadcast, one hit show on cable can transform a network in the minds of viewers, advertisers and distributors.

Fox News was drifting aimlessly until The O’Reilly Factor came along. The same can be said for Comedy Central (The Daily Show), Bravo (Queer Eye For the Straight Guy), TLC (Trading Spaces) and even AMC (Mad Men).

As the cable universe expanded, another revelation dawned: to cut through the noise and clutter, to generate elusive buzz, shows were developed that wilfully paid no heed to overarching network brands.

“The shows that are most successful are probably shows that if you put a list together and said, ‘Match this show to the network,’ you probably would never match them together,” says Bill Carroll, the director of programming at Katz Television Group. “But these shows bring people into the tent.”

This puts OWN in a predicament.

It needs to create a breakout show that can compete at a time when programs such as Keeping Up With the Kardashians, Jersey Shore and Real Housewives get the most attention. But it must also remain faithful to Winfrey’s inspirational mandate.

As Brad Adgate, an analyst with Horizon Media, frames it: “Her brand is very uplifting, nurturing, making you feel good about yourself. Those are her shows. But there is no controversy.”

“I suppose one has to admire her integrity on this,” says Robert Thompson, director of the Bleier Center for Television and Popular Culture at Syracuse University. “But I think she has a very specific sense of what she considers appropriate to put the Oprah Winfrey stamp of approval on. What OWN could desperately use right now is a Real Housewives franchise, a Jersey Shore franchise. Something that gets everyone talking.”

Leavy says the network will never produce down-market shows. Still, he believes there is room on cable for content that is both entertaining and enriching: “We do think there is creative white space there that is still untapped.”

But even if OWN develops a hit or two in the months ahead, there is one final issue: Does Oprah still matter?

“I’ve been studying
television talk shows for a long time,” says Janice Peck, an associate professor at the University of Colorado at Boulder and author of The Age of Oprah: Cultural Icon for the Neoliberal Era.

“And I think one of the biggest things that is going on is that she cannot attract a young audience any more. This was happening even at the end of her show. Her numbers were declining. Her viewers were falling away. And where she was getting hit badly was actually in the younger age ranges.”

During the 1991-92 season, The Oprah Winfrey Show averaged 12.6 million viewers, according to Nielsen. By 2008-2009, that number had plunged by more than half, to 6.2 million.

During this decline, Peck believes Winfrey also alienated parts of her audience by embracing New Age spirituality and endorsing Barack Obama, effectively plunging her into religion and politics during a time of financial upheaval.

“Her message resonated at a particular time,” says Peck. “I don’t think that it has purchase now. It’s like her historical moment has passed. And I don’t think this can be set right.”

If she’s right, there is an irony at play.

As the queen of television, Winfrey has been something of a kingmaker over the years. She’s turned relatively unknown personalities into household names, a list that includes Dr. Phil McGraw, Suze Orman, Dr. Mehmet Oz and Rachael Ray.

Winfrey also revolutionized talk TV, blazing the way for celebrities like O’Donnell and Ellen DeGeneres, to say nothing of the multi-chair gabfests that are now scattered across daytime schedules.

All of her past achievements now stand in the uncertain shadow of OWN.

“What she has said is that building this thing is going to be one of the great challenges of her career,” says Logan. “She’s looking forward to it.”

And so on Monday, when she greets her rapturous fans in Toronto, the story of OWN will be the invisible backdrop. She will lead another Lifeclass for viewers around the globe even as she continues to absorb hard lessons.

Oprah Winfrey has saved many careers and reputations over the years. Now she has to save her own.

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